Outdoor Winter Fun in Boston

How to Enjoy Winter in Boston

8 Outdoor Boston Activities for Winter

Fun Things to Do When Boston Weather Turns Cold

Our recommendations for fun outdoor winter activities in Boston will let you make the most of your visit to Boston during this special time of the year. 

Cold New England weather turns Boston into a sparkling winter wonderland, making it the perfect time to enjoy outdoor winter sports. 

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Our suggestions range from easy things to do on winter days - ice skating on Frog Pond in the middle of the city, or following our itinerary for a scenic walk in the snow - to more challenging: frost-bite sailing!

Maybe you'd like to try skiing or snowboarding down scenic slopes near the city - or pamper yourself in a top New England ski resort.

Whatever your choice, remember:  the best way to love the cold in Boston is to embrace it!

Boston Discovery Guide's Recommendations:   8 Outdoor Activities for Boston Winter Fun 

1.  Skiing near Boston

Skiers on Wachusett Mountain, west of Boston
Skiers on Wachusett Mountain, west of Boston

Less than an hour outside of Boston, you'll find a number of ski areas for downhill skiing, cross-country skiing, snow shoeing, and snow tubing.  Some even have terrain parks for snowboarders and free stylers. 

Go just for the day, or a long weekend.  Most offer lessons and equipment rentals.   

More about Massachusetts ski areas near Boston


2.  Ice Skating in Boston

Ice skating on Boston Common - popular winter activity
Ice skating on Boston's Frog Pond - Popular winter activity

If you're visiting Boston and staying in a hotel in the central part of the city, walk over to Boston Common for ice skating on Frog Pond. 

As you'll see when you get to the rink, this is a popular winter sport in Boston for all ages and all skill levels.  

No need to bring your own skates - just rent them at the rink.  

Don't know how to ice skate?  Also not a problem - for about $10, you can rent a device called a "Bobby Seal" (short for "Bobby the Skating Seal") to hold onto while you learn how to navigate on the ice.

You can also head to several other ice rinks in Boston and Cambridge - most also offer skate rentals and lessons. 

More about ice skating in Boston


3.  Complete Guide to New England Ski Areas

Skiing on Attitash Mountain with spectacular scenery
Skiing on Attitash Mountain with spectacular scenery

New England turns into a skier's paradise from late October through early May. 

Drive just 2 or 3 hours from Boston, and you'll find plenty of places to enjoy this favorite winter activity.  Plus, many mountains and resorts also offer snowboarding, tubing, ice skating, and other winter sports.

Go for the day, or stay for a weekend or longer. 

Check out our complete guide to New England ski areas


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These fun trolley tours, bus tours, and special destinations let you enjoy the best of Boston!


4.  Best New England Ski Vacation Resorts

Loon Mountain, one of New England's top ski resorts
Loon Mountain, one of New England's top ski resorts

New England boasts top-notch ski resorts. 

You'll find excellent accommodations, a variety of skiing options, and plenty of other outdoor and indoor activities designed to appeal to a wide range of interests and ages - ice skating, indoor swimming pools, sleigh rides, tubing, entertainment, and lots more. 

And if your idea of a resort includes spa treatments, gourmet dinners, and luxurious surroundings - well, you can find that too!

Check out our complete guide to New England ski vacation resorts


5.  "Frost Bite" Sailing in Boston

Winter frostbite sailing on the Charles River, with Boston's Esplanade in the background
Winter frostbite sailing on the Charles River, with Boston's Esplanade in the background

"Winter" and "sailing" don't usually go together - but for frigid-weather conditions add to the challenge for avid sailers. 

If you fall into this category, you may want to try when you visit Boston during the winter. 

Many of the Boston sailing centers provide short-term rate options to make this affordable, and lots of camaraderie to make it fun!  

More about sailing in Boston


6.  Sledding on Boston Common

Sledding down a small hill on Boston Common - popular winter activity
Sledding down a small hill on Boston Common

If your kids (or you) just want to have fun in the snow, nothing beats sledding. 

Boston Common's gentle slopes and slightly steeper hills offer the perfect spot whenever freshly-fallen snow blankets the city. 

Ask the concierge at your hotel about the closest place to buy a sled, or something sled-like.  Simple plastic sliders cost $5-$20, and will work fine. 

Boston Common's slopes offer plenty of tree-free spaces, so sledding conditions are reasonably safe even for younger kids.


Top Hotels near Boston Common


7.  Winter Walking Tour Itinerary for Snowy Days

Path along the Esplanade, part of our self-guided winter walking tour itinerary
Path along the Esplanade, part of our self-guided winter walking tour itinerary

Even during Boston's worst winter weather, walking around the city gives you the chance to admire the outlines of trees and buildings against the white snow-covered landscape, plus get some exercise. 

If you happen to visit Boston during or after a snow storm, go out and enjoy the scenery. 

Our self-guided walking itinerary cover about 2.5 miles, and lets you see a variety of lovely sites - but you can easily do just part of it if you want a shorter walk. 

You'll start in the Public Garden, see a bit of the Victorian Back Bay neighborhood, cross Storrow Drive to the Charles River on a scenic overpass, and explore a bit of the frozen Esplanade before ending up back at the Public Garden. 

By then, you'll be ready for a warm drink or meal - so our tour ends with suggestions about fun places to go nearby.

Self-guided winter walking tour itinerary


8.  Running & Jogging in Boston in the Winter

Running along a cleared path on the Esplanade, with the Charles River and Cambridge in the background
Running along a cleared path on the Esplanade, with the Charles River and Cambridge in the background

Dedicated runners don't let a little snow stop them - but ice should, since you don't want your Boston visit to include a trip to a hospital emergency room. 

Avoid the sometimes icy slopes of Beacon Hill (if in any doubt as to why, just look at the photo at the top of the page), and head instead to the relatively flat Esplanade, Public Garden, or Back Bay neighborhood for your run. 

However - even in flat areas, do be very careful about black ice! 

Check out running in Boston in the summer for more suggestions.

Fun Winter Activities in Boston

Best Boston winter activities

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